A skateboard is controlled primarily through the rider's feet. Greater control of a skateboard may be provided by appropriate footwear and allow the rider to perform more skateboard tricks, such as ollies, kickflips, and crooks, with a greater degree of mastery. Any shoe designed for use during skateboarding should be designed to appropriately transmit forces between the rider's foot and the skateboard. In other words, the shoe should be designed to account for the required force transfer used by a skateboard rider to control the skateboard. In addition, the shoe should be designed to provide the rider with a better grip of the skateboard. In particular, the shoe should provide a better grip in the ollie area of the shoe. The skateboard shoes described below provide a structure which provides an appropriate grip between the shoe and a skateboard and facilitates appropriate force transfer between the skateboard and a rider.